Displaying: For Sale
Location: Longboat Key
Property Type(s): Condos
Price: $500,000 to $599,000
Do Not Show Listings
Longboat Key - 21 properties found
4234 GULF OF MEXICO DR #J1, LONGBOAT KEY, FL 34228
$599,00053 Days on yellowkey MLS ID: A4685764
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,273 (2025)Community: Pelican Harbour & Beach ClubCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,273
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: GO and SHOW! Renovated - Waterfront - Pet-Friendly - Discover relaxed coastal living in this beautifully renovated two-bedroom, two-bath bayfront condominium positioned to capture stunning sunrise views over the water. With an open floor plan and expansive bay views from the great room, this residence blends comfort, style and the best of waterfront living. The updated interior features porcelain tile flooring throughout, a bright and airy living space, and a bayfront lanai where you can start your mornings watching the sun rise over the water. The kitchen is equipped with new appliances, and the home also includes in-unit laundry for everyday convenience. Recent improvements provide peace of mind, including a new air-conditioning system, new water heater and hurricane-rated doors. The spacious primary suite offers a private en-suite bath, while the guest suite enjoys direct access to the second bath, creating an ideal layout for family and friends. The condominium is nicely furnished, making it move-in ready. Residents enjoy a full range of resort-style amenities, including private beach access, community pool, tennis courts, pickleball courts, boat docks accommodating vessels up to 28 feet, a clubhouse, organized social activities, bike storage, kayak storage and launch, and on-site maintenance. The well-maintained association has completed numerous recent upgrades, such as new roof, hurricane-rated carports, new docks, freshly painted buildings, and newly re-surfaced tennis and pickleball courts, ensuring long-term value and appeal. You'll also appreciate the association's pet-friendly policy. Association fees include building and flood insurance, cable, water, sewer, trash, escrow reserves, and comprehensive grounds and building maintenance, offering low-maintenance ownership. In a desirable mid-key location, this property is ideal for enjoying the best of island life with exceptional boating, kayaking, and easy access to the bay and Gulf. Whether you’re looking for a full-time residence, seasonal retreat or investment opportunity, this bayfront condominium delivers the ultimate Florida waterfront lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000119 Days on yellowkey MLS ID: A4676925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,041 (2024)Community: Longboat HarbourCondo
Taxes:$6,041
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Sharon Meier (407-927-5669)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000305 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$549,00028 Days on yellowkey MLS ID: A4686987
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $50,000 (8.3%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
4390 EXETER DR #206, LONGBOAT KEY, FL 34228
$529,000186 Days on yellowkey MLS ID: A4670032
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $7,775 (2024)Community: Longboat HarbourCondo
Taxes:$7,775
Remarks: ~~~~~ * * * * SELLER SAYS SELL * * * * ~~~~~~~ * * * * NICEST FULL REMODEL IN LONGBOAT HARBOUR * * * * ~~~~~ PRICED BELOW MARKET VALUE ~~~~~ Enjoy island living nestled in the VIBRANT community of Longboat Harbour on beautiful Longboat Key. This UPDATED and FULLY RENOVATED condo offers a luxurious living experience with abundant amenities and stunning canal views where the Manatee play and sun bathe! Recent tastefully completed renovations include ALL NEW TILE FLOORING, NEW A/C UNIT, a fully updated gourmet kitchen with quartz counters, new cabinets, new appliances, a WASHER/DRYER IN UNIT, fully remodeled bathrooms, new doors and fresh paint throughout, a new primary WALK-IN closet, and PLANTATION SHUTTERS, that provide an interior that is both stylish and inviting. The owners opened the lanai to add more interior space to the living area with a seamless transition. No need to replace the sliders as they did that for you (NEW HURRICANE IMPACT SLIDERS) Need additional storage space? This condo also features a separate storage locker and bike/Kayak storage as well. Located in a prime location within a gated community on Longboat Key, this property is a water-lover's paradise. Boating enthusiasts will appreciate the deep-water canal access to Sarasota Bay, with boat slips available on a first come basis and additional kayak launches. Longboat Harbour is renowned for its welcoming atmosphere and an array of amenities designed to cater to every interest and lifestyle. This resort like community with an on-site manager offers a range of recreational activities including mini-golf, shuffleboard, tennis, and pickleball. Fitness enthusiasts will appreciate the large and well-equipped fitness center, complete with private locker rooms and saunas. Additionally, the beautifully renovated recreation room overlooking the bay, serves as the heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, PRIVATE DEEDED BEACH ACCESS with a cabana, parking, restrooms, and dressing areas. Witness breathtaking sunrises, spot manatees, and savor stunning sunsets from this serene beachfront location. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's most active, social, and vibrant communities! Seize the opportunity to experience waterfront living at its finest. Schedule your private showing today.
Listing Agent: Sheryl Vanduren (720-384-4884)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$585,00060 Days on yellowkey MLS ID: A4684917
REDUCED by $10,000 (1.7%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $8,101 (2024)Community: Longboat HarbourCondo
Taxes:$8,101
Remarks: Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228
$525,00087 Days on yellowkey MLS ID: A4681530
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,901 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,901
Remarks: Luxury Waterfront Living | Proven Income Potential Experience refined coastal living in this pristine, pleasantly updated 2-bedroom, 2-bath residence, offered fully furnished and move-in ready. Enjoy spectacular harbor and Intracoastal water views from both the living room and bedroom, extending to the enclosed lanai—an ideal setting for relaxing mornings and elegant evenings. This residence features an excellent rental history, making it a rare opportunity for investors seeking immediate income, while also serving as a perfect full-time or seasonal retreat. Located in an amenity-rich waterfront community, residents enjoy exclusive access to a private beach club pavilion at 4415 Gulf of Mexico Drive, featuring men’s and women’s restrooms, indoor showers, and optional beach and chair storage. Additional private storage is included on the second floor. Resort-style amenities include four heated swimming pools, a fully equipped fitness center, banquet hall with catering kitchen and dance floor, art studio, billiard and card rooms, and professional on-site management. Boat docks available on a first-come basis with water and electric, accommodating sail or power boats up to 34 feet. Additional highlights include mini golf and a scenic waterfront promenade along the harbor and canal. An exceptional opportunity to enjoy luxurious waterfront living or secure a high-performing investment at an incredibly affordable price point. Schedule your private showing today—this opportunity won’t last.
Listing Agent: Malihe Karimi (941-376-5099)
6700 GULF OF MEXICO DR #117, LONGBOAT KEY, FL 34228
$550,00020 Days on yellowkey MLS ID: A4687787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $2,348 (2025)Community: Whitney BeachSpa: NoCondo
Taxes:$2,348
Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kelly Sallee (941-914-0400)
225 SANDS POINT RD #6103, LONGBOAT KEY, FL 34228
$539,900298 Days on yellowkey MLS ID: A4658152
REDUCED by $29,100 (5.1%) on 04/24/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $6,997 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$6,997
Remarks: Ideal for area residents needing space for overflow guests, or for out-of-state owners who want unlimited use with the ability to still earn income! The most perfectly peaceful lagoon views are enjoyed from this first floor Junior Suite in Building 6. Unlike the other buildings, this building boasts 10' ceilings making it feel especially spacious while optimizing natural light and view. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace overlooking the turquoise lagoon water. Building 6 offers extra privacy as it is located across the street from the main entrance, but still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Updates to the residence include new washer/dryer, new dishwasher, new microwave, new glass shower doors, new commode, new closet shelving, and new fire alarm. This unit is not part of the hotel program; however, it can be rented out by the owner or a 3rd party vendor on a nightly basis. Owners can also become members of the Longboat Key Club to partake in the numerous Resort amenities (Golf, Tennis, Restaurants, Fitness Center, Marina) if they still want to enjoy the benefits of owning in a Resort community without being part of the hotel program.
Listing Agent: Ian Addy, Pa (941-961-8850)
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,00067 Days on yellowkey MLS ID: A4683419
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,183 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,183
Remarks: Discover an exceptional value opportunity in Club Longboat on Longboat Key, one of the island’s most desirable beachside communities known for its active lifestyle and resort style amenities. This three bedroom, two bathroom ground floor walkout residence is currently the least expensive unit in the community and presents a rare chance to create a fully customized coastal retreat. With a solid existing layout and desirable ground level access that enhances indoor / outdoor living, the residence offers tremendous flexibility. Buyers have the opportunity to redesign and expand the third bedroom to add additional square footage, whether to create a more spacious primary suite, an inviting guest retreat, or a dedicated office or flex space. The potential to transform this residence into a personalized showpiece is exceptional. Club Longboat is ideal for tennis, pickleball, and beach enthusiasts, offering eight Har Tru tennis courts with three lined for pickleball, two heated swimming pools, and 750 feet of private Gulf front beachfront complete with lounge chairs and umbrellas. The serene waterfront setting enhances the peaceful atmosphere and scenic surroundings. The residence includes a covered parking space directly in front of the unit along with abundant guest parking. On site management serves the 85 residences, providing convenience and peace of mind within a welcoming, all ages community. Owners enjoy a pet friendly environment with no weight restrictions and a flexible rental policy allowing one month minimum rentals up to twelve times per year, creating excellent income potential. Conveniently located near shopping and fine dining, this is a rare opportunity to secure a value driven property in an amenity rich Longboat Key beachfront community and make it entirely your own.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1932 HARBOURSIDE DR #242, LONGBOAT KEY, FL 34228
$599,00021 Days on yellowkey MLS ID: A4688978
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982Monthly Fee: $81 Tax: $7,099 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$7,099
Elementary School: Southside Elementary
High School: Booker High
Middle School: Pine View School
Remarks: Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.
1912 HARBOURSIDE DR #602, LONGBOAT KEY, FL 34228
$549,900199 Days on yellowkey MLS ID: A4668394
1 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1590 Built: 1982 Tax: $6,146 (2024)Community: Fairway Bay 1Spa: YesCondo
Taxes:$6,146
Remarks: Under contract-accepting backup offers. NEWLY painted bright and fresh INTERIOR. Discover the ideal blend of comfort, convenience, and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key. Enjoy easy access to the gorgeous Gulf beach of Longboat Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active lifestyle. The main level of this townhome offers an open, eat-in kitchen with a breakfast bar that flows effortlessly into the inviting living room, complete with a wood-burning fireplace and large sliding doors leading to a screened lanai with stairs to the outdoors. A convenient half bath completes this level, making it ideal for entertaining. Upstairs, the primary suite features a spacious walk-in closet and a private en-suite bath with double sinks. A second bedroom, also with its full en-suite bath, provides comfort and privacy for guests. The laundry is conveniently on this upper level. On the garage level, you’ll find a large storage room and a bonus space, offering endless possibilities such as a home gym, hobby area or even a space for guests. Fairway Bay homeowners have access to the on-site clubhouse, where there are social activities, a community gym and Har-Tru tennis courts for residents only. Fairway Bay is in Bay Isles, where you have 24/7 gated security and deeded access to the beautiful and private Bay Isles Beach Club. Here you can enjoy gated parking, restrooms, beach chair and umbrella storage, an ice machine, refrigerator and microwave, the ideal place for barbecues, picnics, and sunset gatherings with family and friends. Furniture is included, making this an effortless move-in opportunity to start enjoying the Longboat Key lifestyle from day one. This home is in proximity to Longboat Key Club where you have 45 holes of golf, a world-class tennis center, pickleball courts and five private restaurants accessible to you with additional membership. It’s rare to find a home in Bay Isles offering this level of lifestyle, amenities and value. Don’t miss this opportunity to live your best life on Longboat Key and start making memories of a lifetime today.
Listing Agent: Judy Mitchell (941-275-6838)
600 SUTTON PL #104B, LONGBOAT KEY, FL 34228
$545,000413 Days on yellowkey MLS ID: A4644920
REDUCED by $25,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1973 Tax: $6,737 (2024)Community: Sutton PlaceCondo
Taxes:$6,737
Remarks: Incredible FULL BAY VIEW! This tranquil and beautifully renovated island retreat located in the beach to bay community of Sutton Place offers that and so much more. This 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous, remodeled kitchen is open to the living/dining area across an expanse of granite that includes a custom made dining table with lots of storage underneath and seating all around! Porcelain tile flooring makes the journey from one room to another a seamless and beautiful transition. These smart owners have converted the lanai into finished square footage and it is the perfect spot to enjoy a morning coffee or an evening beverage while watching the fish jump or the birds fly by. They also upgraded to IMPACT RESISTANT SLIDING DOORS AND WINDOWS throughout. The Primary bedroom has this same gorgeous view and a renovated ensuite bath. The once walk-in closet was converted to a small office space, (which could easily be changed back) but it’s current use is rather genius. When guests are not in town, the 2nd bedroom is another tranquil space to enjoy. Did I mention this is a 2 pets friendly community?! Sutton Place also offers its own PRIVATE BEACH CLUB and includes an abundance of amenities including 2 pools, a clubhouse, and an onsite marina with slips for a nominal fee of only $300 per year. The community recently completed a number of updates including repainting, reroofing and passing the milestone inspection and securing a 10 year certification. This owner has paid for all of those upgrades in full. The unit is being offered furnished with exceptions. Here you will find a remarkable quality of laid-back island life but if you're ready for more, enjoy the multitude of restaurants, shopping and the cultural mecca of downtown Sarasota, all within a short drive away.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$598,000199 Days on yellowkey MLS ID: A4667654
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $10,617 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$10,617
Remarks: Exceptional full Bay views, private beach access and kayak launch, and incredible value! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights include hurricane-rated windows and doors, in-unit laundry, a 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.
Listing Agent: Lenore Treiman (941-356-9642)
1932 HARBOURSIDE DR #254, LONGBOAT KEY, FL 34228
$585,000217 Days on yellowkey MLS ID: A4666650
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1192 Built: 1982 Tax: $6,761 (2024)Community: Fairway Bay 1Condo
Taxes:$6,761
High School: Pine View School
Middle School: Booker Middle
Remarks: Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Inside, the kitchen showcases granite countertops and rich wood cabinetry, while both bedrooms are en-suite for privacy and convenience. Lovingly maintained as a part-time vacation retreat since 1989, the condo reflects light use and thoughtful care.Fairway Bay, within Bay Isles, offers a true resort lifestyle with swimming pools, spas, tennis courts, a fitness center, and a welcoming clubhouse for social gatherings. As a Bay Isles resident, you’ll also have access to the private Bay Isles Beach Club, where you can relax on pristine Gulf shores or reserve the clubhouse for special occasions.This coveted location places you within walking distance of a marina, Publix, CVS, and local shops, while just minutes away you’ll find St. Armands Circle (5 miles), downtown Sarasota (8 miles), and all the cultural, dining, and shopping options the Gulf Coast is known for. Bay Isles is also home to 27 holes of championship golf, the world-class Tennis Gardens, the Longboat Key Moorings Marina, and two of the five acclaimed restaurants of the Longboat Key Club—where memberships are available separately. Live every day like you’re on vacation in this exceptional Gulf Coast retreat.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Beverly St Hilaire (818-416-2505)
4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228
$595,000206 Days on yellowkey MLS ID: A4667631
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $9,451 (2024)Community: Windward BayCondo
Taxes:$9,451
Remarks: MOTIVATED SELLER! FULLY FUNDED RESERVES FOR 2026! PET FRIENDLY! NO UPCOMING SPECIAL ASSESSMENTS! 3 BEACH ACCESS POINTS! MILESTONE INSPECTION PASSED! Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views. Every detail has been thoughtfully updated ,this home has been renovated from top to bottom, featuring new flooring, new plumbing, new electrical, new lighting, hurricane-impact windows with shutters for peace of mind and MORE! The brand-new kitchen showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, creating a beautiful space that opens to the bright and airy living area. Both bathrooms have been updated with modern finishes and quarts countertops as well. A Murphy bed in the office area adds versatility, perfect for guests or additional workspace. Enjoy deeded beach access directly across the street for endless days on the sand, or take advantage of boat slips available for residents, ideal for boaters looking to explore Sarasota Bay and the Gulf. Windward Bay is a pet-friendly, amenity-rich community offering multiple pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and walking paths along the bayfront. Perfectly situated near world-renowned restaurants on Longboat Key, St. Armands Circle, and Anna Maria Island, this home combines effortless luxury with the ultimate coastal convenience. Move-in ready and maintenance-free, your Longboat Key lifestyle awaits!
Listing is courtesy of: VRI HOMES (800-531-2885)
Listing Agent: Paulina Vasiliev, Pllc (941-225-5383)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$545,000122 Days on yellowkey MLS ID: A4676730
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? And could you even imagine you could have it for $615,000?! With one owner for the last 29 years, this is your unique opportunity to purchase this fully renovated beachfront walkout 1 bedroom, 1 bath condo in the beach to bay island community of Covert II - and hang onto it like these owners have! With this fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
4234 GULF OF MEXICO DR #D1, LONGBOAT KEY, FL 34228
$595,000154 Days on yellowkey MLS ID: A4673543
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1973Community: Pelican Harbour & Beach ClubCondo
Taxes:
Tax Year:
Remarks: $100,000 PRICE REDUCTION! Refined coastal renovation, waterfront location, deeded beach, pet-friendly, pickleball, tennis, kayaking, boating, and the best of casual island living. Enjoy the larger D1 plan, offering owners more square footage in this open concept two-bedroom, two-bath condominium in Longboat Key's Pelican Harbour & Beach Club. Plus this unit comes totally turnkey furnished and is move-in ready. The Association's amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, bike storage, kayak launch, and owner boat docks. The condominium features include hurricane windows and doors, contemporary-style fireplace, new flooring, custom cabinetry, stainless appliances, crown molding, plantation shutters, tankless water heater, new air conditioner, and designer ceiling fans. Spacious primary suite boasts a private bath with custom walk-in shower, built-in closets, and water views. The guest suite, split from the primary, offers friends and family alike private space and a convenient adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. In addition, with the D1 plan being larger than other Pelican Harbour two-bedroom condominiums, owners will appreciate the larger spaces for gathering and hosting. Association provides on-site maintenance; landscaping; building property, wind, flood and liability insurances; roofs; exterior painting; cable; water; sewer; trash; and more. Pelican Harbour also has fully funded reserves and has installed new roofs, new hurricane-rated carports, upgraded pickleball and tennis courts, and offers owner boat docks with electric and water. Pelican's private beach is only steps away and offers stunning sunset and Gulf views with miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, grocery, restaurants, shopping, places of worship, and easy access to St. Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, larger D1 floor plan, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island. Enjoy Pelican Harbour and Beach Club. Schedule your private showing today.
713 SAINT JUDES DR S #2, LONGBOAT KEY, FL 34228
$595,000122 Days on yellowkey MLS ID: TB8460267
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1215 Built: 1966Community: Saint Judes AptsCondo
Remarks: Exceptional opportunity to own a turnkey, direct waterfront condo with a private dock on Longboat Key, offering 2 bedrooms, 2 bathrooms, 1 carport, 2 parking spaces, and 1,215 sq ft of thoughtfully updated living space. Situated on a quiet canal with direct access to the Intracoastal Waterway, this residence is ideal for those seeking the relaxed, island lifestyle Longboat Key is known for—morning water views, gentle breezes, and peaceful coastal living. The condo has been completely renovated with all improvements fully permitted, providing confidence, comfort, and long-term value. Upgrades include a brand-new kitchen with new appliances, new A/C, new plumbing, new water heater, upgraded electrical panel, and all new windows. The building features a metal roof replaced in 2016, offering durability and added insurance appeal—perfect for buyers looking for low-maintenance, worry-free ownership. Ideally located just minutes from the Gulf of Mexico beaches, island dining, and everyday conveniences, with Durante Park nearby, featuring scenic walking trails, lush gardens, and waterfront views of Sarasota Bay—an ideal setting for daily walks and sunset enjoyment. Unique Opportunity: The adjacent unit is also available, presenting a rare chance to own the entire building as a waterfront duplex—ideal for multi-generational living, hosting visiting family, or creating additional income while enjoying your own private island retreat. Whether you are looking for a full-time residence, seasonal escape, or legacy investment, this beautifully renovated waterfront condo offers the best of Longboat Key living—comfort, tranquility, and timeless coastal appeal. Schedule your private showing today and experience island living at its finest.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Connor Meckley (941-279-0013)
5055 GULF OF MEXICO DR #421, LONGBOAT KEY, FL 34228
$575,000 MLS ID: A4684543
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973Community: Club Longboat Beach & TennisCondo
Remarks: Set within the highly regarded Club Longboat Beach & Tennis on Longboat Key, this 2BR/2BA residence offers an excellent opportunity to create something truly special in one of the island’s most amenity-rich communities. Just under 1,500 sq. ft. and located on the second level, the residence enjoys a comfortable layout where the primary suite opens to a private terrace, bringing in light and breezes throughout the day. The dining area features a tray ceiling and flows easily into the living room, where a full wall of sliders leads to an open terrace and invites indoor and outdoor living to blend naturally. The space is ready for your personal design vision, offering a solid canvas in a location where lifestyle often takes center stage. Life at Club Longboat Beach & Tennis is known for its mix of recreation, flexibility and beachfront access. Residents enjoy 750 feet of pristine shoreline, eight Har-Tru tennis courts, pickleball courts, two heated pools, a fitness center and a relaxed, social atmosphere. Pet-friendly with 2 pets, no weight restrictions and a rental policy allowing one-month minimum stays up to twelve times per year, this residence is ideal for a full-time escape, seasonal retreat or investment opportunity.
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